Hydrogen Peroxide → HCID 13646636, compound

HRID 1732619Notes

Reaction equation

HRID 1732619 reaction equation
[CH3:1][S:2][C:3]1[NH:4][CH:5]=[C:6]([CH2:11][CH2:12][CH2:13][CH3:14])[C:7]=1[N+:8]([O-:10])=[O:9].[OH:15]O>C(O)(=O)C>[CH3:1][S:2]([C:3]1[NH:4][CH:5]=[C:6]([CH2:11][CH2:12][CH2:13][CH3:14])[C:7]=1[N+:8]([O-:10])=[O:9])=[O:15]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 23325026HCID 23325026, compound

Product 1

HCID 13646636HCID 13646636, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Methylthio-3-nitro-4-n-butylpyrrole (3.7g) was suspended in glacial acetic acid (50 ml) and 30% hydrogen peroxide (1.62g) was added. The mixture was heated to 80° for 7 hours, and it was then evaporated to a brown oil. The crude product was purified by column chromatography using silica gel, eluted with benzene and chloroform, to give an oil which crystallized on standing. This was recrystallised from 2-propanol to give 2-methylsulphinyl-3-nitro-4-butyl-pyrrole (1.6g), m.p. 133-4°.

Workup

  1. temperatureThe mixture was heated to 80° for 7 hours
  2. customit was then evaporated to a brown oil
  3. customThe crude product was purified by column chromatography
  4. washeluted with benzene and chloroform
  5. customto give an oil which
  6. customcrystallized
  7. customThis was recrystallised from 2-propanol

Sources & evidence

ORD record
ord-fa5d1093bdbb49d2a05f2ef90a772170
Source dataset
uspto-grants-1980_12
Patent number
US04238494

Reaction notes

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